Pinkie Pie annoys Cranky by trying to guess his name. He eventually reveals his full name, Cranky Doodle Donkey, which sets Pinkie Pie into a song of the same name and has her calling him "Doodle." Angry, Cranky yells at Pinkie, "Nopony calls me Doodle!" Pinkie offers Cranky her friendship, which he refuses, telling Pinkie that he has made enough friends in his life and that he came to Ponyville to settle down and live in peace.

Pinkie tries again, this time using her "Welcome Wagon" to sing a song. However, this backfires when the wagon's burst of confetti blows off Cranky's wig, which Pinkie then steps on believing it to be a spider. Pinkie tries to help by loudly announcing to the crowd that Cranky needs a new wig and points out his baldness. Infuriated and embarrassed, Cranky tries to leave, but Pinkie forces him to go to the local spa in an effort to make it up to him. Afterward, Pinkie presents Cranky with a new, blonde wig. Cranky thanks Pinkie, but he still does not smile.

Later, when Pinkie intrudes on Cranky unpacking at his new, secluded residence, he reveals that he has traveled far and wide across Equestria to various places such as Fillydelphia and Manehattan to search for a special friend of his. While looking through Cranky's belongings, Pinkie accidentally destroys a scrapbook that contains the only physical reminders he has of his special friend. Cranky throws Pinkie out of his house, declaring that he will "never, ever, ever, ever, ever" be her friend.

Determined to apologize, Pinkie returns to Cranky's later. Upon seeing her, Cranky vainly runs and tries to hide from Pinkie. Cranky angrily dismisses Pinkie's apology, telling her that she destroyed the only thing he had to remember his special friend by.

Cranky finally smiles.

Pinkie returns once more with Matilda, whose voice Cranky immediately recognizes. Shocked, he asks how Pinkie could know she is his special friend. Pinkie reveals that she remembered that Matilda has some of the same items in her scrapbook that he had in his. After briefly reminiscing about the night they met at the Grand Galloping Gala and how Matilda left a note for Cranky telling him she was moving to Ponyville (which Cranky never found), Matilda kisses Cranky, causing him to finally smile. Grateful for what she did, Cranky finally accepts Pinkie's offer of friendship but asks that he and Matilda be left alone together for the moment.

A donkey with his design appears briefly in Dragon Quest, ferrying Spike across a river on a raft.

Season four

Season five

Cranky marrying Matilda.

In Slice of Life, Cranky gets married to Matilda. He complains to Derpy about the wedding invitations, and when he loses his toupee before the ceremony, Steven Magnet gives him a replacement made from his mustache.

Personality

True to his name, Cranky is initially easily annoyed and upset. When first introduced, he speaks sarcastically and uses quips. Only once reunited with his "special friend" does Cranky smile and show kindness and joy.

Merchandise

In the Enterplay collectible card game's expansion sets, The Crystal Games card #23 R of Cranky Doodle Donkey has the description, "Nopony calls him Doodle[,]" Absolute Discord card #63 U of Steven Magnet has the description, "This sea serpent made best friends with Cranky Doodle Donkey. If he can pull that off, then he can make friends with ANYPONY[,]" and Absolute Discord card #64 R of Aloe shows Cranky Doodle Donkey.

The Elements of Harmony guidebook

CRANKY DOODLE DONKEY may be a crotchety old grouch who's reluctant to loosen up, but all that changed when the sweet-natured MATILDA came around. Matilda met the cranky mule at the Grand Galloping Gala, where he began courting her as his "special friend." Matilda is the only one who's allowed to call him by the nickname "Doodle."